Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration

被引:25
作者
Groves, Alistair [1 ,2 ]
Sun, Jinwei [1 ,2 ,3 ]
Parke, Hal R. I. [1 ,2 ]
Callingham, Michael [1 ,2 ]
Argent, Stephen P. [2 ]
Taylor, Laurence J. [2 ]
Lam, Hon Wai [1 ,2 ]
机构
[1] Univ Nottingham, GlaxoSmithKline Carbon Neutral Labs Sustainable C, Jubilee Campus,Triumph Rd, Nottingham NG7 2TU, England
[2] Univ Nottingham, Sch Chem, Univ Pk, Nottingham NG7 2RD, England
[3] Nanjing Univ Informat Sci & Technol, Jiangsu Collaborat Innovat Ctr Atmospher Environm, Jiangsu Key Lab Atmospher Environm Monitoring & P, Sch Chem & Mat Sci, Nanjing 210044, Jiangsu, Peoples R China
基金
英国工程与自然科学研究理事会;
关键词
REMOTE FUNCTIONALIZATION; C-C; ARYLBORONIC ACIDS; RHODIUM; ISOMERIZATION; ALLYLATION; 1,3-ENYNES; COMPLEXES; EFFICIENT; REAGENTS;
D O I
10.1039/c9sc06309a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enantioselective synthesis of densely functionalized polycarbocycles by the rhodium(i)-catalyzed reaction of arylboronic acids with 1,3-diketones is described. The key step in these desymmetrizing domino addition-cyclization reactions is an alkenyl-to-aryl 1,4-Rh(i) migration, which enables arylboronic acids to function effectively as 1,2-dimetalloarene surrogates.
引用
收藏
页码:2759 / 2764
页数:6
相关论文
共 44 条
[1]   BIOMIMETIC CONTROL OF CHEMICAL SELECTIVITY [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (06) :170-177
[2]   Zirconocene-assisted remote cleavage of C-C and C-O bonds: application to acyclic stereodefined metalated hydrocarbons [J].
Bruffaerts, J. ;
Pierrot, D. ;
Marek, I. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (44) :10325-10330
[3]   Enantioselective Rhodium-Catalyzed Coupling of Arylboronic Acids, 1,3-Enynes, and Imines by Alkenyl-to-Allyl 1,4-Rhodium(I) Migration [J].
Callingham, Michael ;
Partridge, Benjamin M. ;
Lewis, William ;
Lam, Hon Wai .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) :16352-16356
[4]   Organoboron Initiated Rh-Catalyzed Asymmetric Cascade Reactions: A Subtle Switch in Regioselectivity Leading to Chiral 3-Benzazepine Derivatives [J].
Claraz, Aurelie ;
Serpier, Fabien ;
Darses, Sylvain .
ACS CATALYSIS, 2017, 7 (05) :3410-3413
[5]   Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization [J].
Clarke, Christopher ;
Incerti-Pradillos, Celia A. ;
Lam, Hon Wai .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (26) :8068-8071
[6]   Recent trends in Pd-catalyzed remote functionalization of carbonyl compounds [J].
Franzoni, Ivan ;
Mazet, Clement .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (02) :233-241
[7]   Control of Chemoselectivity by Counteranions of Cationic Palladium Complexes: A Convenient Enantioselective Synthesis of Dihydrocoumarins [J].
Han, Xiuling ;
Lu, Xiyan .
ORGANIC LETTERS, 2010, 12 (01) :108-111
[8]   Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids: 1,4-shift of rhodium from 2-aryl-1-alkenylrhodium to 2-alkenylarylrhodium intermediate [J].
Hayashi, T ;
Inoue, K ;
Taniguchi, N ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) :9918-9919
[9]   Rhodium-Catalyzed Asymmetric Arylative Cyclization of meso-1,6-Dienynes Leading to Enantioenriched cis-Hydrobenzofurans [J].
He, Zhi-Tao ;
Tian, Bing ;
Fukui, Yuki ;
Tong, Xiaofeng ;
Tian, Ping ;
Lin, Guo-Qiang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (20) :5314-5318
[10]   The Isomerization of Allylrhodium Intermediates in the Rhodium-Catalyzed Nucleophilic Allylation of Cyclic Imines [J].
Hepburn, Hamish B. ;
Lam, Hon Wai .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (43) :11605-11610